Benzenesulfonyl chloride → HCID 14720354, compound

HRID 2352005Notes

Reaction equation

HRID 2352005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:9]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH3:10])[S:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:31])=[O:30])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 13652428HCID 13652428, compound

Product 1

HCID 14720354HCID 14720354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 3.5 g. portion of 3-[1-(4-chlorophenylamino)ethyl]pyridine was dissolved in dichloromethane, and 2.7 g. of potassium carbonate and 2.55 ml. of benzenesulfonyl chloride were added. The mixture was stirred at ambient temperature for 1 day, and was then diluted with 10 ml. of dichloromethane and extracted with 20 ml. of aqueous sodium bicarbonate and 20 ml. of water. The organic layer was dried over magnesium sulfate and evaporated under vacuum to an oil. The oil was dissolved in diethyl ether, and the insolubles were separated. The solvent was then evaporated away under vacuum, and the resulting oil was taken up in chloroform and chromatographed over a silica gel column, eluting with chloroform. The product-containing fractions were evaporated to obtain 3.1 g. of the desired product.

Workup

  1. additionwas then diluted with 10 ml
  2. extractionof dichloromethane and extracted with 20 ml
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated under vacuum to an oil
  5. dissolutionThe oil was dissolved in diethyl ether
  6. customthe insolubles were separated
  7. customThe solvent was then evaporated away under vacuum
  8. customchromatographed over a silica gel column
  9. washeluting with chloroform
  10. customThe product-containing fractions were evaporated
  11. customto obtain 3.1 g

Sources & evidence

ORD record
ord-dd6341784dd14f87b95e661dfbea9b88
Source dataset
uspto-grants-1989_10
Patent number
US04874775

Reaction notes

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